TERT-BUTYL N-ALLYLCARBAMATE Chemical Properties

Melting point:

36-38 °C (lit.)

Boiling point:

48-50°C/0.3mm

Density 

0.938 g/mL at 25 °C (lit.)

refractive index 

1.4720 (estimate)

Flash point:

175 °F

storage temp. 

Inert atmosphere,Room Temperature

pka

12.60±0.46(Predicted)

form 

Low Melting Solid

color 

Colorless

Water Solubility 

Insoluble in water. Soluble in methanol.

InChI

InChI=1S/C8H15NO2/c1-5-6-9-7(10)11-8(2,3)4/h5H,1,6H2,2-4H3,(H,9,10)

InChIKey

AWARHXCROCWEAK-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NCC=C

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-36/37/38

Safety Statements 

22-26-36/37/39

RIDADR 

UN 1325 4.1/PG 2

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29241990

MSDS

• Language:English Provider:SigmaAldrich

TERT-BUTYL N-ALLYLCARBAMATE Usage And Synthesis

Chemical Properties

white solid crystalline

Uses

tert-Butyl N-allylcarbamate is used in the synthesis of isoxazolidines. Synthesis of 5-substituted thiazolidin-2-ones is from the reaction of xanthates and tert-butyl N-allylcarbamates .

Synthesis

The synthesis of tert-butyl N-allylcarbamate was carried out as follows: 1. 2.3 mL (30 mmol, 1 eq.) of freshly distilled allylamine was dissolved in 10 mL of dichloromethane (CH2Cl2) in an ice bath (0 °C). 2. 6.54 g (30 mmol, 1 eq.) of di-tert-butyl dicarbonate (Boc2O) dissolved in 20 mL of dichloromethane was slowly added to the above cooled allylamine solution. 3. The reaction mixture was gradually warmed to room temperature with continuous stirring for 4 hours. 4. Upon completion of the reaction, the reaction mixture was diluted with additional dichloromethane and washed sequentially with 5% citric acid solution and brine. 5. The organic layer was separated and dried over anhydrous sodium sulfate (Na2SO4) and subsequently concentrated under vacuum to afford 3.29 g (68% yield) of the target product tert-butyl N-allylcarbamate. Product characterization data: 1H NMR (500 MHz, CDCl3) δ 1.38 (s, 9H), 3.68 (brs, 2H), 4.53 (brs, 1H), 5.02-5.16 (m, 2H), 5.72-5.84 (m, 1H).

References

[1] Tetrahedron Letters, 2007, vol. 48, # 35, p. 6163 - 6166
[2] Angewandte Chemie - International Edition, 2014, vol. 53, # 41, p. 11075 - 11078
[3] Tetrahedron Letters, 1998, vol. 39, # 15, p. 2099 - 2102
[4] Journal of the Chemical Society. Perkin Transactions 1, 2001, # 16, p. 1916 - 1928
[5] Tetrahedron Letters, 2009, vol. 50, # 46, p. 6244 - 6246

TERT-BUTYL N-ALLYLCARBAMATE(78888-18-3)Related Product Information

• Fmoc-D-glutamic acid gamma-tert-butyl ester
• 2-OXO-2,5-DIHYDRO-PYRROLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• BOC-BETA-TBU-D-ALA-OH
• 4-(Aminocarbonyl)-N-[(1,1-dimethylethoxy)carbonyl]-2,6-dimethyl-L-phenylalanine
• (BOC-AMINOOXY)ACETIC ACID
• TERT-BUTOXY ACETIC ACID
• Boc-L-aspartic acid 4-tert-butyl ester
• BOC-D-ALPHA-T-BUTYLGLYCINE
• Boc-D-aspartic acid 4-benzyl ester
• BOC-ALA-GLY-OH
• 3-AMINO-1-[(1,1-DIMETHYLETHOXY)CARBONYL]-3-PIPERIDINEACETIC ACID METHYL ESTER
• tert-butyl 6-hydroxy-3-azabicyclo[3.1.0]hexane-3-carboxylate
• tert-butyl 4-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate
• tert-Butyl 3,8-diazabicyclo[3.2.1]octane-8-carboxylate hydrochloride
• 8-BOC-3,8-DIAZA-BICYCLO[3.2.1]OCTANE
• TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,6-DIHYDROPYRIDINE-1(2H)-CARBOXYLATE
• tert-butyl 2-oxo-6-azaspiro[3.5]nonane-6-carboxylate
• 1-Oxa-7-azaspiro[4.5]decane-7-carboxylic acid, 3-oxo-, 1,1-diMethylethyl ester